Leadership in Indian higher education is now centre stage as a catalyst for massive transformation at a systemic level. Despite several efforts at enhancing leadership among women, we see a phenomenally low number of women at the helm of the affairs in Higher Education. Gender is a cross cutting issue and projects itself as a multi headed hydra in higher education and therefore should be examined from multiple perspectives. There are myriad challenges that women face apart from bearing the double burden of production and reproduction. The structural barriers, institutional and individual mind sets along with lifestyle choices collectively impede women reaching the leadership positions. Structural barriers include lack of access to important informal networks which catapults individuals to higher positions of leadership, and are found missing among women in academia. The stereotypes attached to women such as passionate and nurturing, make matters worse and undermines women’s goal driven, research-based strategies, effort, and power toward higher education. While multiple theories of leadership exist, the higher education sector requires a less hierarchical approach that takes account of its highly specialised and professional context. In order to achieve equality, gender has to be addressed at the forefront. While acknowledging gains made in numbers of women, it is equally significant to address the challenges women continue to confront in reaching and sustaining leadership positions. The gender gap keeps increasing as we cross over to higher positions in the sector and also when we move from so-called soft to hard core disciplines. The paper attempts to examine empirically the barriers, enablers and policies through which substantial transformation can transcend into reality thereby changing the entire landscape of higher education. Women leadership in higher education is an under researched but emerging area with a huge potential for transformation.